Cook the bacon in a large cast iron skillet over medium heat until crispy, flipping when needed to cook the other side. Transfer the cooked bacon to a paper towel-lined plate and blot off the excess grease.
Spread 2 tablespoons of homemade pimento cheese spread on each slice of bread. Leave a small gap near the edges, because the pimento cheese will spread when it melts.
Place two or three slices of bacon on top of the pimento cheese, then put the top slice of bread on each sandwich. Butter the outside of the bread, both top and bottom slices.
Grill one sandwich at a time over medium low heat in a large skillet. Cook until golden brown, then carefully flip it over and grill the other side. Repeat with the other sandwich.
To melt the cheese even more, transfer the sandwiches to a baking sheet and place in a 350°F oven until warmed through.
Transfer to a cutting board and let the sandwiches rest for 5 minutes before cutting in half.
Serve the hot sandwiches with pickle spears, pickled jalapenos, thick tomato slices, and sweet tea.